Oakland Vacations from $366

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Your Oakland Vacation

From its cycling to its walking, there's tons to love about Oakland. Book a customized Oakland vacation package and get ready to fall for the delights of this neighborhood. When it's time to head out and explore, you'll find lots of big-name attractions nearby including Acrisure Stadium, University of Pittsburgh and PNC Park. Tick off one, two or all during your trip to Oakland. No matter your travel plans or budget, booking the ultimate Oakland vacation is simple with Expedia.

The Latest Oakland Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
Downtown Pittsburgh
Price was $487, price is now $366 per person
$366
per person
Mar 6 - Mar 8
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Pittsburgh (PIT)
8.4/10 Very Good! (1,385 reviews)
All in all we had a lovely stay; however there were several things that were broken in the room and the bathroom wallpaper was starting to peel. The shower head sprayed the top of the ceiling if it was turned a specific way and the window shade would not stay raised inhibiting our views. I expected a little bit more from a Hilton property. Also, as a Hilton Honors member, I was shocked to see that only certain levels of members didn’t have to pay for the complementary water. The staff was amazing! And we enjoy the location and food options nearby. Overall a pleasant experience.

Reviewed on Jan 14, 2026

The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
Price was $653, price is now $495 per person
$495
per person
Mar 6 - Mar 8
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Pittsburgh (PIT)
8.6/10 Excellent! (1,003 reviews)
Staff and amenities were great! We loved our room. However, it looks like there were some drinks left in the mini fridge from the patron before us. Other than this, we had a wonderful stay.

Reviewed on Jan 10, 2026

Hampton Inn & Suites North Huntingdon-Irwin

Hampton Inn & Suites North Huntingdon-Irwin

2.5 out of 5
North Huntingdon
Price was $624, price is now $487 per person
$487
per person
Mar 4 - Mar 9
found 23 hours ago
Roundtrip non-stop flight included
Fort Myers (RSW) to Pittsburgh (PIT)
9.4/10 Exceptional! (915 reviews)
The room was clean and stay was quiet. I did pay extra for my dog, the area outside for dogs wasn’t shoveled or salted at any point.

Reviewed on Jan 2, 2026

The Colonial Mt. Lebanon by Luxe PGH

The Colonial Mt. Lebanon by Luxe PGH

3 out of 5
Mount Lebanon
Price was $1,179, price is now $931 per person
$931
per person
Mar 3 - Mar 8
found 22 hours ago
Roundtrip flight included
Fort Myers (RSW) to Pittsburgh (PIT)
2/10 (2 reviews)
Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Price was $620, price is now $493 per person
$493
per person
Apr 10 - Apr 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Pittsburgh (PIT)
7.6/10 Good! (37 reviews)
Kitchen was fully equipped with everything you would need. The rooms were clean and spacious, beautiful building and friendly staff. Parking is what you would expect in a downtown area but was very easy and the attendant was great.

Reviewed on Jan 14, 2026

Where to stay in Oakland

Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland
Downtown Pittsburgh which includes a bridge and a river or creek

Downtown Pittsburgh

2 out of top 10 points of interest in this area
4.5/5(2,251 area reviews)

Discover the urban downtown center, home to historic sites like Point State Park and the Cultural District. Enjoy diverse shopping options and easy access to public transportation, including the "T" light rail and bus networks.

Find hotels in Downtown Pittsburgh

Oakland Hotel Deals

Courtyard by Marriott Pittsburgh University Center

Courtyard by Marriott Pittsburgh University Center

3.5 out of 5
100 Lytton Avenue Pittsburgh PA
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $139 total per night from Jan 21 to Jan 22
$139 total
Jan 21 - Jan 22
Total with taxes and fees
9/10 Wonderful! (576 reviews)
Clean rooms, courteous staff

Reviewed on Jan 13, 2026

Courtyard by Marriott Pittsburgh University Center
Residence Inn Pittsburgh Oakland/University Place

Residence Inn Pittsburgh Oakland/University Place

3 out of 5
3341 Forbes Ave Pittsburgh PA
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $139 total per night from Feb 1 to Feb 2
$139 total
Feb 1 - Feb 2
Total with taxes and fees
9/10 Wonderful! (926 reviews)
From reservation to stay everything went really well. Ideal location to highway, restaurants, etc. Room had everything we needed. Loved the kitchenette.

Reviewed on Jan 13, 2026

Residence Inn Pittsburgh Oakland/University Place
The Oaklander Hotel, Autograph Collection

The Oaklander Hotel, Autograph Collection

4.5 out of 5
5130 Bigelow Boulevard Pittsburgh PA
Fully refundableReserve now, pay when you stay
$195 nightly
The price is $222 total per night from Feb 5 to Feb 6
$222 total
Feb 5 - Feb 6
Total with taxes and fees
9.2/10 Wonderful! (736 reviews)
Yes as to bar. I did not have breakfast.

Reviewed on Jan 11, 2026

The Oaklander Hotel, Autograph Collection
See all 1,888 properties in Oakland
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Oakland

Oakland featuring a garden

University of Pittsburgh

4.5/5(843 reviews)

Enjoy the collegiate vibe around University of Pittsburgh, a top college in Pittsburgh. Stroll along the riverfront or experience the acclaimed theater scene in this vibrant area.

University of Pittsburgh
Carnegie Museum of Natural History which includes interior views and views

Carnegie Museum of Natural History

4.5/5(48 reviews)

From rare jaguars to geological marvels and ancient fossils, you’ll find it all at this Pittsburgh institution, one of the country’s largest natural history museums.

Carnegie Museum of Natural History
Carnegie Museum of Art featuring art, a statue or sculpture and interior views

Carnegie Museum of Art

5/5(4 reviews)

If you like your art with a modern twist, you’re in for a treat at this exceptional museum, which also features impressive furniture and architecture galleries.

Carnegie Museum of Art

Things to do

Pittsburgh Pirates Baseball Game at PNC Park

Pittsburgh Pirates Baseball Game at PNC Park

$65
per adult
Pittsburgh Pirates Baseball Game at PNC Park
Pittsburgh Penguins Ice Hockey Game at PPG Paints Arena

Pittsburgh Penguins Ice Hockey Game at PPG Paints Arena

$97
per adult
Pittsburgh Penguins Ice Hockey Game at PPG Paints Arena
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl

Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl

$13
per adult
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl
See all activities in Pittsburgh

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.